You're making a lot of outside-view arguments, but I'm taking an inside-view with my website (I think I have enough information to take an inside view).
It's like the map and the territory - inside-view is like looking at a lower-level map. So it's like we're looking at two different maps. Your interpretation of your higher level map may be correct, but the lower level map might have more information that leads to a different answer.
Right now, I'm working on a big comparison of my site, to all of my competitors. Comparing what my site has to what they have. I hope to be done in the next few days, and I'll let you know when I am and show you what I've got. I think it'll make more sense once I could show it to you, and I think it'll allow for a more productive discussion. (Note: I should have done this explicit comparison earlier on, like immediately. I'm very disappointed in myself for not doing so. Like this has been the most disappointed I've been in myself in over a year probably. Thanks for taking the time to discuss this with me.)
My motivation behind this post stems from Aumann's agreement theorem. It seems that my opinions on startups differ from most of the rationality community, so I want to share my thoughts, and hear your thoughts, so we could reach a better conclusion.
I think that if you're smart and hard working, there's a pretty good chance that you achieve financial independence within a decade of the beginning of your journey to start a startup. And that's my conservative estimate.
"Achieve financial independence" only scratches the surface of the benefits of succeeding with a startup. If you're an altruist, you'll get to help a lot of other people too. And making millions of dollars will also allow you the leverage you need to make riskier investments with much higher expected values, allowing you to grow your money quickly so you could do more good.
A lot of this is predicated on my belief that you have a good chance at succeeding if you're smart and hardworking, so let me explain why I think this.
Along the lines of reductionism, "success with a startup" is an outcome (I guess we could define success as a $5-10M exit in under 10 years). And outcomes consist of their components. My argument consists of breaking the main outcome into it's components, and then arguing that the components are all likely enough for the main outcome to be likely.
I think that the 4 components are:
The Idea
Your idea has to be for a product or service (I'll just say product to keep things simple) that creates demand, and can be met profitably. In other words, make something people want (this article spells it out pretty well).
What could go wrong?